Ni-catalyzed regioselective C–C bond formation of 1,1-disubstituted allenes with aldehydes
Literature Information
Publication Date
2023-12-11
DOI
10.1039/D3QO01800H
Impact Factor
5.281
Authors
Seoyeon Kim, Jinyoung Kim, Shrikant D. Tambe, Eun Jin Cho
View Original
Abstract
Allenes, despite their structural resemblance to alkenes and alkynes, exhibit unique reactivity due to the orthogonal arrangement of their cumulative π-bonds, making precise allene selectivity an emerging area of interest. Previous studies on Ni-catalyzed coupling reactions between allenes and aldehydes yielded diverse regioselectivities, with nucleophilic and reductive conditions producing different outcomes. In this work, we developed a regioselective method for generating linear products through coupling at the terminal carbon of 1,1-disubstituted allenes using photoredox/Ni-dual catalysis. We achieved the regioselectivity by strategically modifying substrate patterns and the catalytic system employing an unconventional P^N ligand. This work represents a notable advancement in selective catalysis, offering valuable insights into the control of allene reactivity.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![2-Methyl-2-propanyl {3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-oxetanyl}carbamate structure](https://static.chemtradehub.com/structs/127/1279090-25-3-1b84.webp "2-Methyl-2-propanyl {3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-oxetanyl}carbamate structure")
2-Methyl-2-propanyl {3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-oxetanyl}carbamate
CAS Number:
1279090-25-3
Molecular Formula:
C20H30BNO5
N-(5-Fluoro-2-oxo-2,3-dihydro-4-pyrimidinyl)benzamide
CAS Number:
10357-07-0
Molecular Formula:
C11H8FN3O2
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